Zinc-mediated chain extension reaction of 1,3-diketones to 1,4-diketones and diastereoselective synthesis of trans-1,2-disubstituted cyclopropanols

Article abstract of DOI:10.1021/jo051950b

A variety of 1,3-diketones can be efficiently converted into the corresponding 1,4-diketones and trans-1,2-disubstituted cyclopropanols by using organozinc species in one-pot reactions. It was found that 2.3 equiv of CF ₃CO₂ZnCH₂I was effective to give the corresponding chain-extended products in 44-85% yields, while a mixture of organozinc species formed from 4.0 equiv of Et₂Zn, 2.0 equiv of CF₃CO₂H, and 4.0 equiv of CH₂I₂ resulted in the formation of trans-1,2-disubstituted cyclopropanols with quite good yields and diastereoselectivity.